Specionin

Base Information

• Chemical Name: Specionin
• CAS No.: 87946-74-5
• Deprecated CAS: 97101-25-2
• Molecular Formula: C20H26O8
• Molecular Weight: 394.41564
• DSSTox Substance ID: DTXSID50450672
• Nikkaji Number: J230.932G
• Wikidata: Q27108316
• Mol file: 87946-74-5.mol

Synonyms:Specionin;(-)-Specionin;Specionin, (-)-;87946-74-5;CHEBI:9214;96944-53-5;Benzoic acid, 4-hydroxy-, 2,4-diethoxyoctahydro-1a-(hydroxymethyl)oxireno(4,5)cyclopenta(1,2-c)pyran-6-yl ester, (1aS-(1aalpha,1bbeta,2alpha,4beta,5abeta,6beta,6aalpha))-;[(1S,2S,4S,5S,6R,8S,10S)-8,10-diethoxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.02,4]decan-5-yl] 4-hydroxybenzoate;C09799;DTXSID50450672;C20-H26-O8;Q27108316

Chemical Property of Specionin

Chemical Property:

• PSA: 106.98000
• LogP: 1.43900
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 394.16276778
• Heavy Atom Count: 28
• Complexity: 562

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1CC2C(C(O1)OCC)C3(C(C2OC(=O)C4=CC=C(C=C4)O)O3)CO
• Isomeric SMILES: CCO[C@@H]1C[C@@H]2[C@H]([C@H](O1)OCC)[C@@]3([C@H]([C@H]2OC(=O)C4=CC=C(C=C4)O)O3)CO

Technology Process of Specionin

There total 193 articles about Specionin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester (121784-84-7) → (-)-specionin (87946-74-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 3h;

DOI:10.1139/v94-271

Reference yield:

(2S-cis)-2-ethoxy-3,6-dihydro-2H-pyran-3-acetic acid, methyl ester (109669-17-2) → (-)-specionin (87946-74-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 81 percent / LDA

2: 85 percent / LDA

3: 1.) p-ClC₆H₄NCO, Et₃N, 2.) m-CPBA / 1.) 110 deg C, 3.) benzene, 80 deg C

4: 42 percent / (i-Bu)2nBuAlH, Li⁽¹⁺⁾

5: 72 percent / DMAP, Et₃N

6: 77 percent / 3,5-DNPBA, Na₂HPO₄ / CH₂Cl₂

7: 57 percent / H₂, B(OH)3 / Rh-Al / methanol; H₂O

8: 70 percent / CH₃SO₂Cl, Et₃N

9: 93 percent / LAH / tetrahydrofuran / -78 °C

10: 64 percent / RuH₂(PPh₃)4 / ethanol

11: 61 percent / DCC, DMAP

12: 70 percent / 1.) Hg(OAc)2, 2.) NaBH₄, NaOH

13: 1.) TBAF, 2.) H₂ / 2.) Pd/C / 1.) THF

With dmap; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; mercury(II) diacetate; tetrabutyl ammonium fluoride; lithium cation; hydrogen; boric acid; p-chlorphenylisocyanate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; dihydridotetrakis(triphenylphosphine)ruthenium; rhodium on aluminium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00251a044

Reference yield:

<2S-<2α,3α(R*)>>-2-ethoxy-3,6-dihydro-3-(1'-thiophenyl)-2H-pyran-3-acetic acid, methyl ester (109686-28-4,121681-23-0,121681-24-1,121681-27-4,121703-61-5) → (-)-specionin (87946-74-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / LDA

2: 1.) p-ClC₆H₄NCO, Et₃N, 2.) m-CPBA / 1.) 110 deg C, 3.) benzene, 80 deg C

3: 42 percent / (i-Bu)2nBuAlH, Li⁽¹⁺⁾

4: 72 percent / DMAP, Et₃N

5: 77 percent / 3,5-DNPBA, Na₂HPO₄ / CH₂Cl₂

6: 57 percent / H₂, B(OH)3 / Rh-Al / methanol; H₂O

7: 70 percent / CH₃SO₂Cl, Et₃N

8: 93 percent / LAH / tetrahydrofuran / -78 °C

9: 64 percent / RuH₂(PPh₃)4 / ethanol

10: 61 percent / DCC, DMAP

11: 70 percent / 1.) Hg(OAc)2, 2.) NaBH₄, NaOH

12: 1.) TBAF, 2.) H₂ / 2.) Pd/C / 1.) THF

With dmap; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyl-diisobutylaluminum hydride; 3,5-dinitrobenzoperoxoic acid; mercury(II) diacetate; tetrabutyl ammonium fluoride; lithium cation; hydrogen; boric acid; p-chlorphenylisocyanate; methanesulfonyl chloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium diisopropyl amide; palladium on activated charcoal; dihydridotetrakis(triphenylphosphine)ruthenium; rhodium on aluminium; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1021/ja00251a044

upstream raw materials:

ethanol

endo-2-(hydroxymethyl)-exo-2,3-epoxy-cis-bicyclo<3.3.0>octa-7-en-exo-4-yl 4-hydroxybenzoate

4-Benzyloxy-benzoic acid (1aS,1bS,2S,4S,5aR,6S,6aS)-1a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2,4-diethoxy-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

4-Hydroxy-benzoic acid (1aS,1bS,5aR,6S,6aS)-2,4-diethoxy-1a-hydroxymethyl-octahydro-1,3-dioxa-cyclopropa[a]inden-6-yl ester

Refernces

• 1、 Leonard, John,Hussain, Nigel. "Total Synthesis of (+/-)-Specionin". . p. 61 - 70. Retrieved 2007/10/02.
• 2、 Whitesell, James K.,Allen, Diane, E.. "Total Synthesis of (-)-Specionin". . p. 3583 - 3588. Retrieved 2007/10/02.